The Dynamo’s last CONCACAF Champions League appearance was in 2013, a year before vice president and general manager Matt Jordan joined the team.

But Jordan, who played professionally for 13 seasons, is familiar with the competition, having been a part of one of the most storied runs in its existence.

As a goalkeeper for the Montreal Impact late in his career in 2009, he led the team to the quarterfinals of the Champions League — a first for a Canadian team. It defeated Mexican club Santos Laguna 2-0 in the first leg before falling in the second match of the two-leg series.

In 2014, this time as a member of the Impact’s front office, Jordan returned to the quarterfinals again; this time witnessing the team’s improbable run through to the final, where it ultimately lost to Mexican powerhouse Club América.

“We’re very excited about the draw. We know it’s going to be a very challenging match up,” Jordan said of Monday’s drawing, which will pit the Dynamo against Guatemalan club CD Guastatoya in February.

“I’ve been fortunate enough to be a part of it as a player and working in the front office and I’m just so excited that we’re a part of this competition in Houston now. It’s exciting for us as a club and we’re really looking forward to it.”

In reality, the Dynamo’s preparations for the competition began after they defeated the Philadelphia Union to win the U.S. Open Cup to qualify in September. But with the drawing concluded, preparations are ramping up.

“From a front office front office perspective right now, we’re focused on getting everything buttoned up form a logistical standpoint. We’re already looking at different flight patterns and how that will blend with our preseason plans,” Jordan said. “I think the next month for us, the focus will be on our roster and continuing to look at our current roster and always looking to improve.”

That roster was good enough to win the domestic Cup—although the Dynamo failed to qualify for the MLS playoffs. But against some of the top clubs from around North America, some additions may be necessary.

Additionally, the timing of the competition presents an added challenge for MLS teams, who begin their seasons just a month after the Dynamo’s Round of 16 match begins.

“They’re in the middle of their seasons while we’re in the beginning of our season and our preparation so that’s where we’re going to need to be able to hit the ground running,” Jordan said. “It’s a tough balancing act. The preparations and the workload and the practice planning between our coaching staff and our sports science department, this is where it becomes really important.”

While some Dynamo players departed the country to be closer to their families in the offseason, others have stayed and spend extra time training at their facility about 10 miles south of BBVA Compass Stadium.

“For myself, you’re used to playing the same teams two, three times a year, and now you’re playing a team that you don’t know much about going into it,” said Dynamo defender A. J. DeLaGarza, who experienced the competition during his time with the L.A. Galaxy.

“It’s challenging and I think you can see it a bit on the national level, unfortunately. It’s tough to go to these countries and get a result. That first leg is going to be crucial. No matter who it is, we have to be ready for a battle physically and mentally.”

It’s those differences, an unfamiliar opponent in unfamiliar territory, that adds to the thrill for Jordan.

“These games in the Champions League just have a totally different feel,” he said. “It’s important to expect the unexpected. You’re playing in different conditions, on different types of fields, in different types of stadiums and playing in different environments. That’s what’s beautiful about this competition and that’s what makes it so intriguing.”

Glynn A. Hill covers Rice and Houston-area college athletics for the Houston Chronicle, joining the paper in September 2015. A graduate of Howard University, he previously worked internships at organizations including the Associated Press and USA Today.